The present invention relates to an active energy ray-curable polyimide resin composition excellent in thermal resistance, solubility in solvent, and moisture resistance under a high temperature and capable of development with a dilute alkali aqueous solution. More specifically, it relates to an active energy ray-curable polyimide resin composition most suitably usable as patterning materials including various negative resists such as a solder resist, a plating resist, or a resist for an insulating layer of a printed circuit board in build-up process or a semiconductor device.
Since active energy ray-curable resins to be cured with ultraviolet ray or electron beam exhibit a high curing rate and are preferable in view of the protection of the environment, a substitution thereof for the conventional thermosetting resins or thermoplastic resins is in progress. Under the circumstances, improvement of thermal resistance and electric properties of the active energy ray-curable resins is demanded in various fields. At present, the active energy ray-curable resins include a wide variety of resins such as ester acrylate resins, epoxy acrylate resins, urethane acrylate resins, and the like, but there is a limitation especially on the improvement of thermal resistance.
As an active energy ray-curable resin having an improved thermal resistance, Japanese Patent Laid-Open No. 344889/2000 discloses a process for producing an active energy ray-curable polyimide resin which comprises reacting a trifunctional or more functional aromatic carboxylic acid and/or anhydride thereof, a polyisocyanate compound, and a compound having a polymerizable double bond and a hydroxyl group and/or an epoxy group. In the publication, there are descriptions that a polyimide resin excellent in thermal resistance, solubility in solvent, curability with an active energy ray, and developing property is obtained, a biuret compound or nurate compound can be used as the polyisocyanate compound to be used in the process, and an aliphatic or alicyclic polyisocyanate is preferred because an imide resin excellent in solubility in solvent and curability is obtained. Moreover, the Examples of the publication disclose a process for producing a polyimide resin using an alicyclic diisocyanate as the polyisocyanate compound.
However, although the polyimide resin obtained in the Examples of the above Japanese Patent Laid-Open No. 344889/2000 has a better thermal resistance as compared with ester acrylate resins, epoxy acrylate resins, urethane acrylate resins and the like, there remains a problem that the resistance is not sufficient yet.
An object of the invention is to provide an active energy ray-curable polyimide resin composition having a sufficient thermal resistance, capable of patterning with a dilute alkali aqueous solution, and also capable of using a common organic solvent, for example, a polar solvent having neither nitrogen atom nor sulfur atom as a solvent.
Other objects and effects of the invention will become apparent from the following description.
In consideration of the above problems, as a result of extensive studies, the present inventors found that a polymerizable polyimide resin (I) having an isocyanurate ring, an alicyclic structure, and a (meth)acryloyl group and capable of pattering with a dilute alkali aqueous solution is a resin exhibiting particularly good thermal resistance and excellent solubility in organic solvent and capable of patterning with a dilute alkali aqueous solution as well as exhibiting excellent moisture resistance even at a high temperature of 120xc2x0 C. or higher, and that an active energy ray-curable polyimide resin composition suitable for the use as a resist or the like can be easily obtained by incorporating the resin. Based on the findings, the invention has been completed.
Namely, the invention provides an active energy ray-curable polyimide resin composition which comprises a polymerizable polyimide resin (I) having an isocyanurate ring, an alicyclic structure, an imide ring, and a (meth)acryloyl group, and being capable of patterning with a dilute alkali aqueous solution.